Ammonium Hydroxide → 6-Chloro-4-(trifluoromethyl)pyridin-2-amine

HRID 2382765Notes

Reaction equation

HRID 2382765 reaction equation
[CH:1]1[C:6]([Cl:7])=[N:5][C:4](Cl)=[CH:3][C:2]=1[C:9]([F:12])([F:11])[F:10].[OH-].[NH4+:14]>>[Cl:7][C:6]1[N:5]=[C:4]([NH2:14])[CH:3]=[C:2]([C:9]([F:12])([F:11])[F:10])[CH:1]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 5209682,6-Dichloro-4-(trifluoromethyl)pyridine

Product 1

HCID 139868176-Chloro-4-(trifluoromethyl)pyridin-2-amine

Procedure

A solution of 2,6-dichloro-4-(trifluoromethylpyridine) (Fluorochem, 10.0 g; 46.30 mmol; 1.0 eq.) in ammonium hydroxide (˜25% in water) (40.0 mL; 4.0 V) was heated to 180° C. for 3 h in a Parr apparatus and cooled down to rt. After this time, reaction mixture was filtered over a bed of celite, evaporated to dryness under reduced pressure, triturated with DCM and filtered. The mother liquors were concentrated under reduced pressure to give the title compound as a yellow oil that crystallized upon standing (4.83 g; 53%). HPLC, Rt: 3.58 min. (purity 96.9%). LC/MS, M+(ESI): 196.8, M−(ESI): 194.8.

Workup

  1. customAfter this time, reaction mixture
  2. filtrationwas filtered over a bed of celite
  3. customevaporated to dryness under reduced pressure
  4. customtriturated with DCM
  5. filtrationfiltered
  6. concentrationThe mother liquors were concentrated under reduced pressure

Sources & evidence

ORD record
ord-45729c4144484b268c2ec4b77c475f92
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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